Derivative of aminoarylarsinic acid.



v are employed in theforinoi doses of up to 1} ,gr.

nwiirnn swims PATENT QFFiCE PAUL EHRLICH AND ALFRED BERTHEIM, or ERAN FonTon-T nE-eizim, GERMANY,

ASSIGNORS TQ FARBWERKE VORM.

THE-MAIN, GERMANY, A CORPORATION OF GERMANY,

DERIVATIVE OF AlVIIN'OARYLARS INIC ceases.

No Drawin g.

can be obtained by treatingthemwith cy anic acid or its esters. The compounds thus obtained correspond to the constitutioial formula:

in which "Rarepresentsan alkyl, aryl or hydrogen, and tl1611'l0Im3t1OI1 corresponds to the equation: p NHOONHR These new compounds. are of therapeutical value ininl'ectious diseases caused by thetrypanosomasandalso in s philis. They alkali salts by subcutaneous tallinc products, being blo in hot water, insoluble in ether and benzene and also in diluted alkalies. l/Vith the latter they form readily soluble crystalline salts. f

The procedure for manufacturing the new compounds may for instance be as follows:

(320 gr; of sodium salt of p-aminophenylarsmic acid are dissolved'in 8.6 liters .of'water and to the cold solution are then added 380 gr. of potassium cyanate. The solution thus obtained is mixed with 480 gr. of glacialacetic acid and allowed to stand for about 24 hours at ordinary temperature.- Thereupon the new compound, which may be termed carbmninoarsanilic acid, is precipitatcd by means of 1560 ccm. of hydrochloric acid (specific carbaminoarsanilic aci can be filtered ofl",

Specification of Letters I atent. Application filediiugust m, 1908. Serial No. 448,255. (Siiccimens) aniinoai'ylarsinicv acids, for

their neutral injections of They are white 'crys difficultlyrsoluble in cold water and alcohol, more readily soluacids, but soluble in gravity 1.124). The

- Patented Oct. 2c, 1909.

recrystallized from water, thus being purilied, and afterward dried. It is easily sol'uble in hot water but diflicultly soluble in alcohol, and insolubl'e in ether and benzene.

y Combined'with caustic Soda or sodium carbonate it forms a sodium salt which is read ily solulolein water and which crystallizes in small prisms. The acid decomposes when heated to over 180 C, assuming at the same time a dark color. In the same way similar compounds can be produced from other instance, 0- methyl-p-aminophenylarsiinic acid yielding with isocyanic acid o-methyl pecarbaminoaminophen ylarsinic acid, which decomposes when heated 'to'aboutBOO", (L; also if, in-

stead of isocyanic acid,"its""esters are combined with aminoarylarsinic acids, thus for instance p-aminophenylarsinic acid ielding with .1r =etl1yl-'isocyanate i and' pheny' -isocyanate, respectively, methylcarhaminoarsanilic acid, decomposing at about 200. 0., and phenylcarbaminoarsanilic acid, which stands atemperature of 2401'Q, but decomposes when heated in a test tube by a flame.

' Having now described our invention, what we claim isz. v .1. new products, the compounds the constitution of which corresponds to the formula in, which R represents an. ,alkyl, aryl or hydrogen, being derivativesof aminoarylarsinic acids, white crystalline products which are difficultly soluhlein cold water or'alcoh'ol, more readily soluble in hot wa ter', insoluble in ether, benzeneand diluted acids, which decompose ath-igher temperature assuming then. adark color, and which form with ftlkfillBS salts readilysoluble 111 water. I

2. As a new product, the compound the corresponds to the I constitution of which formula I NHCONH2 being a derivative of p-aminophenylarsinic acid, a white crystalline compound which is acids, which when heated to over 180 2 amma In testimony whereof, we afiix our signatures m presence of two wltnesses.

,P AULEHRLIOH. ALFRED BERTHEIM.

Witnesses:

JEAN GRUND, CARL GRUND. 

